The father of modern trading built and lost several fortunes over his career, famously shorting the 1929 crash for what would be worth over $3 billion today, only to lose it all again in the years that followed.
Jesse Livermore
Launch
1877
Death / Exploit
1940
Total Loss
Fortune rebuilt and lost 4 times
Livermore made and lost multiple fortunes, most famously profiting enormously from the 1929 crash before later losses and personal struggles led to his death by suicide in 1940.